Spiro[17H-dicyclopropa[6,7:15,16]cyclopenta[a]phenanthren-17,2'(5'H)-furan]-3,5'(2H)-dion, 1,3',4',6,7,8,9,10,11,12,13,14,15,16,20,21-Hexadecahydro-10,13-dimethyl-, [6R-(6α,7α,8β,9α,10β,13β,14α,15α,16α,17β)]-

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H360：Kann die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen.

• Sicherheit

  P201：Vor Gebrauch besondere Anweisungen einholen.

  P202：Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P308+P313：BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

  P405：Unter Verschluss aufbewahren.

  P501：Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Drospirenone Chemische Eigenschaften,Einsatz,Produktion Methoden

• Beschreibung

  The steroid drospirenone in combination with the estrogen agonist ethinylestradiol was introduced in Germany as a new oral contraceptive for women. This analog of the aldosterone antagonist spironoiactone can be synthesized in five steps from 3β-hydroxy- 15β,16β-methylene-5-androsten-l7-one. Since its binding profile for steroid receptors is very similar to progesterone, drospirenone mimics the progestogen agonistic activity as well as the anti-androgenic and anti-mineralocorticoid properties of the endogenous hormone. In rats, drospirenone inhibited ovulation at 6.3 mglkglday p.o. Compared with currently available progestins which lack anti-mineralocorticoid activity, drospirenone did not cause weight gain that could result from fluid retention in clinical studies. Its combination with ethinylestradiol was well tolerated and did not engender adverse effects on blood pressure or plasma lipid levels. Drospirenone is rapidly absorbed in man with an oral bioavailability of 76%. It is extensively metabolized since over 20 different metabolites were observed in the urine and in the feces, resulting for instance from hydrolysis of the lactone in the plasma or reductive conjugation of the enone to the 3-sulfate ester of 45 dihydrodrospirenone. Its elimination is bi-exponential with an initial and a terminal half-life of 2 and 25-33h respectively.

• Beschreibung

  Drospirenone is a synthetic progestogen that binds to the progesterone, mineralocorticoid, and androgen receptors with binding affinities of 20, 230, and 65% relative to R5020, aldosterone , and R1881, respectively. In vivo, drospirenone inhibits spontaneous ovulation in rats (ID₅₀s = 0.3-1.0 mg/day) when administered orally or subcutaneously. Drospirenone (0.5 mg/animal) administered six times per day maintains pregnancy in ovariectomized pregnant rats. It reduces serum testosterone (Item Nos. 15645 | ISO60154) and luteinizing hormone in cynomolgus monkeys in a dose-dependent manner. Drospirenone (10 mg/animal per day) also inhibits testosterone-induced growth of the seminal vesicles and prostate in castrated rats. Formulations containing drospirenone have been used as oral contraceptives.

• Chemische Eigenschaften

  Off-White Crystalline Powder

• Originator

  Schering AG (Germany)

• Verwenden

  anti-cancer therapeutic

• Verwenden

  antiviral

• Verwenden

  Synthetic progestogen exhibiting antimineralocorticoid and antiandrogenic activity.

• Verwenden

  Drospirenone has been used as a progestogen agent in pond snail and fish.

• Definition

  ChEBI: Drospirenone is a steroid lactone and a 3-oxo-Delta(4) steroid. It has a role as a contraceptive drug, an aldosterone antagonist and a progestin.

• Manufacturing Process

  2.75 g of trimethyl sulfoxonium iodide is stirred in 57 ml of dimethyl sulfoxide with 341 mg of 80% sodium hydride oil suspension for 2 h at room temperature. The almost clear solution is combined under nitrogen with 2.0 g of 15α,16α-methylene-3-oxo-4,6-androstadiene-[17(β-1')-spiro- 5']perhydrofuran-2'-one and agitated for 24 h at room temperature. The mixture is then stirred into ice water, the thus-obtained precipitate is filtered off, washed with water, and taken up in methylene chloride. After drying and evaporation, the residue is purified by repeated preparative layer chromatography, thus obtaining 520 mg of 6β,7β,15α,16α-dimethylene-3-oxo- 4-androstene-[17(β-1')-spiro-5']perhydrofuran-2'-one (drospirenone).

• Trademarks

  Yasmin

• Therapeutic Function

  Aldosterone antagonist

• Allgemeine Beschreibung

  Drospirenone, 3-oxo-6β,7β:15β,16β-dimethylene-17α-pregn-4-en-21,17-carbolactone,differs structurally from all the other commercially availableprogestins. Its structure is similar to that of spironolactone,an MR antagonist, and it does have antimineralocorticoidactivity as well as progestational activity. It isalso reported to have some antiandrogenic effects. Thespirolactone at C17 and the two cyclopropyl groups at C6-C7 and C15-C16 contribute to these unique actions.Drospirenone is the progestin component in the newer oralcontraceptives, Yasmin and Yaz, and in the HRT product,Angeliq.

• Biochem/physiol Actions

  Drospirenone is a fourth-generation progestin that has antimineralocorticoid, and antiandrogenic activity in addition to potent progestogenic activity. In two recent studies drospirenone appeared to double the risk of venous thromboembolism compared to levonorgestrel, although other studies found little added risk.

Drospirenone Upstream-Materialien And Downstream Produkte

Spiro[17H-dicyclopropa[6,7:15,16]cyclopenta[a]phenanthren-17,2'(5'H)-furan]-3,5'(2H)-dion, 1,3',4',6,7,8,9,10,11,12,13,14,15,16,20,21-Hexadecahydro-10,13-dimethyl-, [6R-(6α,7α,8β,9α,10β,13β,14α,15α,16α,17β)]- Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global(435)Suppliers

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